Are we making a difference? Is our programming achieving the intended outcomes? Should we continue investing in these strategies, or is it time to adjust course? For any mission-driven organization, these are essential questions about impact. They are in fact existential questions. If an organization isn’t making progress toward its mission, there are serious questions about sustainability.
Why Monitoring Progress in a Dynamic Environment Matters
In a dynamic environment—where the pace of change is fast and the context is complex—monitoring the organization’s progress is crucial. These dynamic environments call on leaders to adopt a navigational mindset and approach. Outside Angle’s co-founder Sam Franklin describes the navigational approach as this: “It involves having a vision for where you are going, and then regularly pausing to evaluate progress. Hypotheses are tested, and big challenges are broken down into smaller tasks. Action is constantly taken on doing the next thing.”
In these types of environments, it can be very difficult to “lock in” on a set of metrics for monitoring the team’s progress because so much is changing and uncertain. However, that’s what makes it all the more necessary. When everything around you feels like an amorphous, complicated blob, the most successful teams find a way to grab on and get clear about where they are today so they know what to do next.
How to Monitor Progress through Evolutions and Change: Five Lessons to Learn From
In our work with organizations of various sizes and across sectors, we have learned a few things about what does and doesn’t work to monitor progress in a dynamic environment.
One of our long-time clients, WPS Institute, is the exemplar—so much so, that it’s worth giving a look into their approach so that others can learn from them. In 2022, WPS Institute developed a new strategic vision for advancing models of schooling where learning thrives everywhere, in classrooms and beyond; where students are empowered to shape their own educational journeys; and where entire communities contribute to the development of young people. The vision was clear, but the matter of “how” the team would do it relied on a number of hypotheses and assumptions that they would need to explore in practice.
Today, the team has successfully partnered with three Massachusetts school systems to redesign aspects of middle school, piloted and launched innovative student leadership programs with out-of-school-time partners, and harnessed valuable R&D that they share with educators nationally.
Lesson 1: Don’t Wait to Get Started
Decide what matters most and make a plan to measure it.
- What outcomes are you after?
- What do you want to learn?
- What progress is critical to see as you work your way toward the big mission of the organization?
It can be tempting to boil the ocean. Don’t let the perfect be the enemy of the good. Start with a basic framework, and get moving. Choose a mix of interim indicators (things that you can notice change in and respond to immediately) as well as long-term outcomes that you expect to see change in over time.
WPS Institute began by leveraging our Success and Sustainability Framework as a place to begin. Over time, their progress monitoring framework has evolved and matured with them, and it’s most certainly more attuned to their needs today than when we began three years ago. Getting started early has served them well—as the work provided them concrete evidence of impact around which to build a case for continuation and expansion.
Lesson 2: Measure Progress with Fidelity and Rigor
The saying goes, “you get what you put in.” WPS Institute has gained value from their progress monitoring approach in large part because of the fidelity and rigor with which they gather data and evidence.
This team of curious learners enjoys getting their hands on the data. They have long partnered with Transcend and leveraged their Leaps Student Voice Survey as a core tool for measuring student relevance, connection, and agency. They also use interview protocols to hear from students, using prompts such as “I used to think… and now I think…” Twice a year, the team gathers data and slices it in different ways, looking for meaningful differences between student groups that can point toward action steps. More recently, the team has begun to use AI to surface themes across lengthy interview transcripts, reducing the time spent on data processing and freeing up time for the critical “so what, now what” conversations.

Lesson 3: Make It a Team Effort
In a dynamic environment, a collaborative and constructive team culture can help teams navigate almost anything they face. By fostering open communication, trust, and collaboration, teams can respond quickly to changes, adapt their strategies, and make progress collectively. Involving the entire team (or the full leadership team in the case of bigger organizations) in the work builds engagement and interest in the data insights. This work includes selecting metrics that matter, gathering data, and contributing content to the progress dashboard. Progress monitoring can, in fact, be a culture-strengthening process, if done collaboratively.
For WPS Institute, progress monitoring involves the entire team. Everyone has a role in collecting and analyzing data. Practically speaking, this approach works because it divides up the responsibility. More importantly though, it also makes this work an intentional point of collaboration and shared responsibility. The data becomes “theirs” to share and learn from, not something that belongs to just “the research guy.”
Lesson 4. Use the Data for All Its Worth
We can all relate to the goal of working smarter, not harder. For any team investing in progress monitoring, it’s important to leverage the data for all its worth. The data—and a cyclical approach to having repeated, reflective conversations to review it—can help a team sharpen its vision, prioritize actions, notice positive bright spots and worrisome hot spots, and communicate progress with stakeholders.
WPS Institute has done a great job of making the most of the progress data. During semiannual retreats, the team surfaces lessons learned and calls attention to areas signaling a need for attention. Bright spots are lifted up to the board and partners, and developed into case studies and content for publication. Most recently, the team contrasted the journeys and specific needs of two different partners based on the trends in the data, which led to a productive conversation about their approach and change management strategies. Intense bursts of activity happen twice each year to collect and assemble the data, but then the data is available throughout the year for all sorts of uses.
Lesson 5. Stay Open and Curious
Progress in a dynamic environment is not just about achieving set goals and milestones. It is about adaptability, resilience, and the ability to seize new opportunities as they arise. Continuous progress monitoring can, over time, reveal new connections and ideas that weren’t on the roadmap, yet provide opportunity and purpose for the next phase of work.
One of the things we love most about the WPS Institute team is the ways in which curiosity guides their individual behaviors and their organizational culture. They are intentional about learning. Equally important, they don’t hold things precious or fear constructive criticism. The team values the data, and follows where it leads them. This culture didn’t just appear overnight: it’s a clear output of a psychologically safe space for authentically interrogating progress and collectively charting each new chapter of the journey.

Conclusion
Monitoring progress in a dynamic environment requires a shift in mindset. It is not just about achieving predefined goals and KPIs. It’s about embracing change, seizing opportunities, and fostering a collaborative culture. By having a standardized approach to measurement and focusing on what matters most, while remaining flexible and adaptive, teams can effectively navigate the challenges and opportunities that a dynamic environment presents.
